Mohammed Fremoule, 29 of Cazenove Road, Walthamstow was captured on CCTV outside the busy City of London station.
Dressed completely in black he sneaked up from behind on the victim, who was wearing red shorts and in conversation with a female, and pulled the expensive watch from the man's wrist.
Fremoule pleaded guilty to robbery and handling stolen goods and was sentenced at Inner London Crown Court.
He received two years and eight months.
He was arrested on March 29 after he was found in possession of a stolen mobile phone.
The watch, which was uninsured, was never recovered.
Detective Constable Marcus Fairclough, of the City of London Police, said: “This was a callous and opportunistic robbery, carried out against a vulnerable victim who was already suffering from a broken ankle.
“The offender targeted him, stalked him outside Liverpool Street Station and then violently ripped a watch worth approximately £28,000 from his wrist, before making off.“Due to our extensive CCTV network, we were able to capture the incident and trace the suspect’s movements.
“Working closely with colleagues from the Metropolitan Police Service (MPS) and the British Transport Police (BTP), we were able to build the evidence needed to bring him before the courts.
“This sentence sends a clear message that those who come to the City to commit crime will be relentlessly pursued.
“Through our investigations, partnerships and world-class CCTV coverage, we are identifying offenders, bringing them to justice and helping to keep the City’s streets safe by locking up criminals who pose a threat to the public.”



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